Arylamine compound and organic light-emitting device including the same

ABSTRACT

Provided are an arylamine compound and an organic light-emitting device including the same.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority from and the benefit of Korean PatentApplication No. 10-2019-0058307, filed on May 17, 2019, which is herebyincorporated by reference for all purposes as if fully set forth herein.

BACKGROUND Field

Exemplary embodiments of the invention relate to an arylamine compoundand an organic light-emitting device including the same.

Discussion of the Background

Organic light-emitting devices are self emissive devices that producefull-color images, and, compared with devices of the related art, theyhave a wide viewing angle, a high contrast ratio, and a short responsetime, and show excellent characteristics in terms of luminance, drivingvoltage, and response speed.

In an example, an organic light-emitting device may include a firstelectrode disposed on a substrate, and a hole transport region, anemission layer, an electron transport region, and a second electrode,which are sequentially disposed on the first electrode. Holes providedfrom the first electrode may move toward the emission layer through thehole transport region, and electrons provided from the second electrodemay move toward the emission layer through the electron transportregion. Carriers, such as holes and electrons, recombine in the emissionlayer to produce excitons. These excitons transit from an excited stateto a ground state, thereby generating light.

The above information disclosed in this Background section is only forunderstanding of the background of the inventive concepts, and,therefore, it may contain information that does not constitute priorart.

SUMMARY

One or more exemplary embodiments include an arylamine compound having anovel structure and an organic light-emitting device including the same.

Additional features of the inventive concepts will be set forth in thedescription which follows, and in part will be apparent from thedescription, or may be learned by practice of the inventive concepts.

One or more exemplary embodiments provide an arylamine compoundrepresented by Formula 1:

In Formula 1,

R₁ to R₁₄ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —C(═O)(Q₁), —N(Q₁)(Q₂), P(═O)(Q₁)(Q₂), and—S(═O)₂(Q₁)(Q₂),

at least one substituent of the substituted C₅-C₆₀ carbocyclic group,the substituted C₁-C₆₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀ heterocycloalkyl group,the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₁-C₆₀ heteroaryl group, the substitutedC₁-C₆₀heteroaryloxy group, the substituted C₁-C₆₀heteroarylthio group,the substituted monovalent non-aromatic condensed polycyclic group, andthe substituted monovalent non-aromatic condensed heteropolycyclic groupmay be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, and

a distance d between a center of an A′ phenyl group and a center of a Bphenyl group may be a distance by which orbitals of the A′ phenyl groupand the B phenyl group may overlap each other.

One or more exemplary embodiments may also provide an organiclight-emitting device including: a first electrode; a second electrodefacing the first electrode; and an organic layer between the firstelectrode and the second electrode and including an emission layer,wherein the organic layer includes at least one heterocyclic compoundrepresented by Formula 1.

It is to be understood that both the foregoing general description andthe following detailed description are exemplary and explanatory and areintended to provide further explanation of the invention as claimed.

BRIEF DESCRIPTION OF THE DRAWINGS

The accompanying drawings, which are included to provide a furtherunderstanding of the invention and are incorporated in and constitute apart of this specification, illustrate exemplary embodiments of theinvention, and together with the description serve to explain theinventive concepts.

FIG. 1 is a schematic view of a structure of an organic light-emittingdevice according to an embodiment.

FIG. 2 is a schematic view of a structure of an organic light-emittingdevice according to another embodiment.

FIG. 3 is a schematic view of a structure of an organic light-emittingdevice according to another embodiment.

FIG. 4 is a schematic view of a structure of an organic light-emittingdevice according to another embodiment.

DETAILED DESCRIPTION

In the following description, for the purposes of explanation, numerousspecific details are set forth in order to provide a thoroughunderstanding of various exemplary embodiments or implementations of theinvention. As used herein “embodiments” and “implementations” areinterchangeable words that are non-limiting examples of devices ormethods employing one or more of the inventive concepts disclosedherein. It is apparent, however, that various exemplary embodiments maybe practiced without these specific details or with one or moreequivalent arrangements. In other instances, well-known structures anddevices are shown in block diagram form in order to avoid unnecessarilyobscuring various exemplary embodiments. Further, various exemplaryembodiments may be different, but do not have to be exclusive. Forexample, specific shapes, configurations, and characteristics of anexemplary embodiment may be used or implemented in another exemplaryembodiment without departing from the inventive concepts.

Unless otherwise specified, the illustrated exemplary embodiments are tobe understood as providing exemplary features of varying detail of someways in which the inventive concepts may be implemented in practice.Therefore, unless otherwise specified, the features, components,modules, layers, films, panels, regions, and/or aspects, etc.(hereinafter individually or collectively referred to as “elements”), ofthe various embodiments may be otherwise combined, separated,interchanged, and/or rearranged without departing from the inventiveconcepts.

The use of cross-hatching and/or shading in the accompanying drawings isgenerally provided to clarify boundaries between adjacent elements. Assuch, neither the presence nor the absence of cross-hatching or shadingconveys or indicates any preference or requirement for particularmaterials, material properties, dimensions, proportions, commonaltiesbetween illustrated elements, and/or any other characteristic,attribute, property, etc., of the elements, unless specified. Further,in the accompanying drawings, the size and relative sizes of elementsmay be exaggerated for clarity and/or descriptive purposes. When anexemplary embodiment may be implemented differently, a specific processorder may be performed differently from the described order. Forexample, two consecutively described processes may be performedsubstantially at the same time or performed in an order opposite to thedescribed order. Also, like reference numerals denote like elements.

When an element, such as a layer, is referred to as being “on,”“connected to,” or “coupled to” another element or layer, it may bedirectly on, connected to, or coupled to the other element or layer orintervening elements or layers may be present. When, however, an elementor layer is referred to as being “directly on,” “directly connected to,”or “directly coupled to” another element or layer, there are nointervening elements or layers present. To this end, the term“connected” may refer to physical connection, with or withoutintervening elements. For the purposes of this disclosure, “at least oneof X, Y, and Z” and “at least one selected from the group consisting ofX, Y, and Z” may be construed as X only, Y only, Z only, or anycombination of two or more of X, Y, and Z, such as, for instance, XYZ,XYY, YZ, and ZZ. As used herein, the term “and/or” includes any and allcombinations of one or more of the associated listed items.

Although the terms “first,” “second,” etc. may be used herein todescribe various types of elements, these elements should not be limitedby these terms. These terms are used to distinguish one element fromanother element. Thus, a first element discussed below could be termed asecond element without departing from the teachings of the disclosure.

Spatially relative terms, such as “beneath,” “below,” “under,” “lower,”“above,” “upper,” “over,” “higher,” “side” (e.g., as in “sidewall”), andthe like, may be used herein for descriptive purposes, and, thereby, todescribe one elements relationship to another element(s) as illustratedin the drawings. Spatially relative terms are intended to encompassdifferent orientations of an apparatus in use, operation, and/ormanufacture in addition to the orientation depicted in the drawings. Forexample, if the apparatus in the drawings is turned over, elementsdescribed as “below” or “beneath” other elements or features would thenbe oriented “above” the other elements or features. Thus, the exemplaryterm “below” can encompass both an orientation of above and below.Furthermore, the apparatus may be otherwise oriented (e.g., rotated 90degrees or at other orientations), and, as such, the spatially relativedescriptors used herein interpreted accordingly.

The terminology used herein is for the purpose of describing particularembodiments and is not intended to be limiting. As used herein, thesingular forms, “a,” “an,” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise. Moreover,the terms “comprises,” “comprising,” “includes,” and/or “including,”when used in this specification, specify the presence of statedfeatures, integers, steps, operations, elements, components, and/orgroups thereof, but do not preclude the presence or addition of one ormore other features, integers, steps, operations, elements, components,and/or groups thereof. It is also noted that, as used herein, the terms“substantially,” “about,” and other similar terms, are used as terms ofapproximation and not as terms of degree, and, as such, are utilized toaccount for inherent deviations in measured, calculated, and/or providedvalues that would be recognized by one of ordinary skill in the art.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this disclosure is a part. Terms,such as those defined in commonly used dictionaries, should beinterpreted as having a meaning that is consistent with their meaning inthe context of the relevant art and should not be interpreted in anidealized or overly formal sense, unless expressly so defined herein.

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawings, wherein like referencenumerals refer to like elements throughout. In this regard, the presentembodiments may have different forms and should not be construed asbeing limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the figures, toexplain aspects of the present description. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items. Expressions such as “at least one of,” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list.

An embodiment of the inventive concepts provides an arylamine compoundrepresented by Formula 1:

Formula 1 will be described in detail below.

R₁ to R₁₄ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —C(═O)(Q₁), —N(Q₁)(Q₂), P(═O)(Q₁)(Q₂), and—S(═O)₂(Q₁)(Q₂).

at least one substituent of the substituted C₅-C₆₀ carbocyclic group,the substituted C₁-C₆₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀ heterocycloalkyl group,the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₁-C₆₀ heteroaryl group, the substitutedC₁-C₆₀heteroaryloxy group, the substituted C₁-C₆₀heteroarylthio group,the substituted monovalent non-aromatic condensed polycyclic group, andthe substituted monovalent non-aromatic condensed heteropolycyclic groupmay be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃—Ccycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃—Ccycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

A distance d between a center of an A′ phenyl group and a center of a Bphenyl group is a distance by which orbitals of the A′ phenyl group andthe B phenyl group may overlap each other.

The distance d between the center of the A′ phenyl group and the centerof the B phenyl group may be controlled by adjusting at least oneselected from the substituents R₁ to R₁₄ in Formula 1. For example, thedistance d may be controlled by adjusting at least one selected from thesubstituents R₁ to R₄ of the A phenyl group, for example, R₂ or R₃, orthe distance d may be controlled by adjusting at least one selected fromthe substituents R₅ to R₉ in the C is phenyl group, for example, R₆ orR₇. In one embodiment, the distance d may be controlled by adjusting atleast one selected from the substituents R₁₀ to R₁₄ of the B phenylgroup. In one embodiment, the distance d may be controlled by adjustingat least two selected from the substituents of the A phenyl group, thesubstituents of the B phenyl group, or the substituents of the C phenylgroup.

For example, the d between the center of the A′ phenyl group and thecenter of the B phenyl group may be in a range of about 3 Å to about 5Å.

In one embodiment, at least one selected from R₂, R₃, R₆, and R₇ may bea substituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, or a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,or at least one selected from R₂ and R₃ may be a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, or a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In one embodiment, at least one selected from R₂, R₃, R₆, and R₇ may beselected from a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, abiphenyl group, a terphenyl group, a pentalenyl group, an indenyl group,a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, apentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, an isoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, aquinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a dihydroacridinyl group, aphenanthrolinyl group, a phenazinyl group, a dihydrophenazinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, abenzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, atetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, atriazinyl group, a carbazolyl group, a dibenzofuranyl group, adibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolylgroup, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, anaphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranylgroup, a dinaphthothiophenyl group, a dinaphtho silolyl group, animidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinylgroup, a thiazolopyridinyl group, a benzonaphthyridinyl group, anazafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolylgroup, an azadibenzofuranyl group, an azadibenzothiophenyl group, anazadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolylgroup, an indeno carbazolyl group, and an indolocarbazolyl group, eachunsubstituted or substituted with at least one selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, an n-propylgroup, an isopropyl group, an n-butyl group, a sec-butyl group, anisobutyl group, a tert-butyl group, an ethenyl group, a prophenyl group,a butenyl group, a methoxy group, an ethoxy group, an n-propoxy group,an isopropoxy group, an n-butoxy group, a sec-butoxy group, an isobutoxygroup, and a tert-butoxy group.

In one embodiment, the other(s) among R₂, R₃, R₆, and R₇, having noselected substituents and R₁, R₄, R₅, and R₈ to R₁₄ may eachindependently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, or a substituted or unsubstitutedC₁-C₂₀ alkyl group.

In one embodiment, at least one selected from R₂, R₃, R₆, and R₇ may beselected from groups represented by Formulae 3-1 to 3-16:

In Formulae 3-1 to 3-16,

Y₁₁ may be O, S, C(Z₁₃)(Z₁₄), N(Z₁₃), or Si(Z₁₃)(Z₁₄),

Z₁₁ to Z₁₄ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkenyl group, a C₁-C₂₀ alkynyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a biphenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a triperylenylgroup, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, and atriazinyl group.

p3 may be an integer from 1 to 3, p4 may be an integer from 1 to 4, p5may be an integer from 1 to 5, p6 may be an integer from 1 to 6, and p9may be an integer from 1 to 9. * indicates a binding site to aneighboring atom.

In one or more embodiments, at least one selected from R₂, R₃, R₆, andR₇ may be selected from groups represented by Formulae 4-1 to 4-21:

In one embodiment, the compound of Formula 1 may be represented by oneselected from Formulae 2-1 to 2-4:

In one embodiment, in Formulae 2-1 to 2-4, BG may be a substituentrepresented by one selected from Formulae 3-1 to 3-16.

In one embodiment, in Formulae 2-1 to 2-4, BG may be a substituentrepresented by one selected from Formulae 4-1 to 4-21.

In one embodiment, the arylamine compound may be represented by oneselected from Formulae 1 to 16:

In the arylamine compound, triplet-triplet annihilation (TTA) may causereverse intersystem crossing. Accordingly, the arylamine compound may beused as a TTA fluorescence material. In the arylamine compound, reverseintersystem crossing may change energy existing in a triplet state to asinglet state. Thus, it is possible to obtain external quantumefficiency (EQE) higher than the EQE of a general fluorescent dopant.Although not intended to be limited to a theory, in the arylaminecompound represented by Formula 1, the distance d between the center ofthe A′ phenyl group and the center of the B phenyl group is a distanceat which the orbitals of the A′ phenyl group and the B phenyl group mayoverlap each other, and thus, it is considered that reverse intersystemcrossing caused by TTA is possible. At this time, the distance d betweenthe center of the A′ phenyl group and the center of the B phenyl groupmay be controlled by the substituents of the arylamine compound.

The arylamine compound may also be used as, in addition to thefluorescent dopant, a fluorescent or phosphorescent host.

At least one arylamine compound represented by Formula 1 organiclight-emitting device may be used between a pair of electrodes of anorganic light-emitting device. For example, the arylamine compound maybe included in at least one selected from a hole transport region, anelectron transport region, and an emission layer. In one or moreembodiments, the arylamine compound represented by Formula 1 may be usedas a material for a capping layer located outside a pair of electrodesof an organic light-emitting device.

Accordingly, another embodiment of the inventive concepts provides anorganic light-emitting device including: a first electrode; a secondelectrode facing the first electrode; and an organic layer disposedbetween the first electrode and the second electrode and including anemission layer, wherein the organic layer includes at least onearylamine compound represented by Formula 1.

The expression “(an organic layer) includes at least one arylaminecompound” as used herein may include a case in which “(an organic layer)includes identical arylamine compounds” or a case in which “(an organiclayer) includes two or more different arylamine compounds”.

For example, the organic layer may include, as the arylamine compound,only Compound 1. In this regard, Compound 1 may exist only in theemission layer of the organic light-emitting device. In one or moreembodiments, the organic layer may include, as the arylamine compound,Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 mayexist in an identical layer (for example, Compound 1 and Compound 2 mayall exist in an emission layer), or different layers (for example,Compound 1 may exist in an emission layer and Compound 2 may exist in anelectron transport region).

In one embodiment, the first electrode may be an anode, the secondelectrode may be a cathode, and the organic layer may further include ahole transport region between the first electrode and the emission layerand an electron transport region between the emission layer and thesecond electrode.

The hole transport region may include a hole injection layer, a holetransport layer, an emission auxiliary layer, an electron blockinglayer, or any combination thereof. The electron transport region mayinclude a buffer layer, a hole blocking layer, an electron controllayer, an electron transport layer, an electron injection layer, or anycombination thereof.

In one embodiment, the emission layer of the organic light-emittingdevice may include the arylamine compound.

In one or more embodiments, the arylamine compound included in theemission layer of the organic light-emitting device may be afluorescence emitter having triplet-triplet annihilation (TTA)characteristics, and accordingly, the emission layer may emit TTAfluorescence.

In one or more embodiments, the emission layer of the organiclight-emitting device may include a host and a dopant. The host mayinclude the arylamine compound, and the dopant may include aphosphorescent dopant or a fluorescent dopant.

In one or more embodiments, the emission layer may consist of thearylamine compound; or the emission layer may further include a host.Here, an amount of the arylamine compound in the emission layer may bein a range of about 0.1 parts by weight to about 50 parts by weightbased on 100 parts by weight of the emission layer.

The host included in the emission layer may include at least oneselected from an anthracene-based compound, a pyrene-based compound, aspiro-bifluorene-based compound, a carbazole-based compound, abenzimidazole-based compound, and a phosphine oxide-based compound.

In one embodiment, the emission layer of the organic light-emittingdevice may include the arylamine compound, and the emission layer mayemit light having a maximum emission wavelength of about 440 nm or moreand about 650 nm or less.

In one embodiment, the hole transport region in the organiclight-emitting device may have a lowest unoccupied molecular orbital(LUMO) energy level of less than −3.5 eV.

In one embodiment, the electron transport region in the organiclight-emitting device may include at least one selected from a phosphineoxide-based compound and a benzimidazole-based compound, and may furtherinclude an alkali metal, alkaline earth metal, a rare earth metal, analkali metal compound, alkaline earth metal compound, a rare earth metalcompound, an alkali metal complex, alkaline earth metal complex, a rareearth metal complex, or any combination thereof.

The term “organic layer” as used herein refers to a single layer and/ora plurality of layers disposed between the first electrode and thesecond electrode of the organic light-emitting device. A materialincluded in the “organic layer” is not limited to an organic compound.

FIG. 1 is a schematic cross-sectional view of an organic light-emittingdevice 10 according to an embodiment. The organic light-emitting device10 includes a first electrode 110, an organic layer 150, and a secondelectrode 190.

Hereinafter, the structure of the organic light-emitting device 10according to an embodiment and a method of manufacturing the organiclight-emitting device 10 will be described in connection with FIG. 1.

[First Electrode 110]

In FIG. 1, a substrate may be additionally disposed under the firstelectrode 110 or above the second electrode 190. The substrate may be aglass substrate or a plastic substrate, each having excellent mechanicalstrength, thermal stability, transparency, surface smoothness, ease ofhandling, and water resistance.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming the first electrode 110 on the substrate. When thefirst electrode 110 is an anode, the material for forming the firstelectrode 110 may be selected from materials with a high work functionto facilitate hole injection.

The first electrode 110 may be a reflective electrode, asemi-retransmissive electrode, or a transmissive electrode. When thefirst electrode 110 is a transmissive electrode, a material for formingthe first electrode 110 may be selected from indium tin oxide (ITO),indium zinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and anycombinations thereof, but embodiments of the present disclosure are notlimited thereto. In one or more embodiments, when the first electrode110 is a semi-transmissive electrode or a reflective electrode, amaterial for forming the first electrode 110 may be selected frommagnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li),calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), andany combinations thereof, but embodiments of the present disclosure arenot limited thereto.

The first electrode 110 may have a single-layered structure, or amulti-layered structure including two or more layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO,but the structure of the first electrode 110 is not limited thereto.

[Organic Layer 150]

The organic layer 150 may be disposed on the first electrode 110. Theorganic layer 150 may include an emission layer.

The organic layer 150 may further include a hole transport regionbetween the first electrode 110 and the emission layer and an electrontransport region between the emission layer and the second electrode190.

[Hole Transport Region in Organic Layer 150]

The hole transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The hole transport region may include at least one layer selected from ahole injection layer, a hole transport layer, an emission auxiliarylayer, and an electron blocking layer.

For example, the hole transport region may have a single-layeredstructure including a single layer including a plurality of differentmaterials, or a multi-layered structure having a hole injectionlayer/hole transport layer structure, a hole injection layer/holetransport layer/emission auxiliary layer structure, a hole injectionlayer/emission auxiliary layer structure, a hole transportlayer/emission auxiliary layer structure, or a hole injection layer/holetransport layer/electron blocking layer structure, wherein for eachstructure, constituting layers are sequentially stacked from the firstelectrode 110 in this stated order, but the structure of the holetransport region is not limited thereto.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound representedby Formula 201, and a compound represented by Formula 202:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

L₂₀₅ may be selected from *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₂-C₂₀ alkenylene group, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xa1 to xa4 may each independently be an integer from 0 to 3,

xa5 may be an integer from 1 to 10, and

R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independently be selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 202, R₂₀₁ and R₂₀₂ may optionally be linked viaa single bond, a dimethyl-methylene group, or a diphenyl-methylenegroup, and R₂₀₃ and R₂₀₄ may optionally be linked via a single bond, adimethyl-methylene group, or a diphenyl-methylene group.

In one embodiment, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xa1 to xa4 may each independently be 0, 1,or 2.

In one or more embodiments, xa5 may be 1, 2, 3, or 4.

In one or more embodiments, R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independentlybe selected from:

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described above.

In one or more embodiments, at least one selected from R₂₀₁ to R₂₀₃ inFormula 201 may each independently be selected from:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a phenyl group substituted with a C₁-C₁₀ alkylgroup, a phenyl group substituted with —F, a naphthyl group, a fluorenylgroup, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, in Formula 202, i) R201 and R202 may belinked via a single bond, and/or ii) R203 and R204 may be linked via asingle bond.

In one or more embodiments, at least one selected from R₂₀₁ to R₂₀₄ inFormula 202 may be selected from:

a carbazolyl group; and

a carbazolyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, acarbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

The compound represented by Formula 201 may be represented by Formula201A

For example, the compound represented by Formula 201 may be representedby Formula 201A(1), but embodiments of the present disclosure are notlimited thereto:

In one embodiment, the compound represented by Formula 201 may berepresented by Formula 201A-1, but embodiments of the present disclosureare not limited thereto:

In one embodiment, the compound represented by Formula 202 may berepresented by Formula 202A:

In one or more embodiments, the compound represented by Formula 202 maybe represented by Formula 202A-1:

In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1,

L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ are the same asdescribed above,

R₂₁₁ and R₂₁₂ may each independently be the same as defined inconnection with R₂₀₃, and

R₂₁₃ to R₂₁₇ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group.

The hole transport region may include at least one compound selectedfrom Compounds HT1 to HT39, but embodiments of the present disclosureare not limited thereto:

A thickness of the hole transport region may be from about 100 Å toabout 10,000 Å, for example, about 100 Å to about 1,000 Å. When the holetransport region includes at least one selected from a hole injectionlayer and a hole transport layer, a thickness of the hole injectionlayer may be from about 100 Å to about 9,000 Å, for example, about 100 Åto about 1,000 Å, and a thickness of the hole transport layer may befrom about 50 Å to about 2,000 Å, for example about 100 Å to about 1,500Å. When the thicknesses of the hole transport region, the hole injectionlayer, and the hole transport layer are within these ranges,satisfactory hole transporting characteristics may be obtained without asubstantial increase in driving voltage.

The emission auxiliary layer may increase light-emission efficiency bycompensating for an optical resonance distance according to thewavelength of light emitted by an emission layer, and the electronblocking layer may block the flow of electrons from an electrontransport region. The emission auxiliary layer and the electron blockinglayer may include the materials as described above.

[p-Dopant]

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant.

In one embodiment, the p-dopant may have a LUMO energy level of lessthan −3.5 eV.

The p-dopant may include at least one selected from a quinonederivative, a metal oxide, and a cyano group-containing compound, butembodiments of the present disclosure are not limited thereto.

In one embodiment, the p-dopant may include at least one selected from:

a quinone derivative, such as tetracyanoquinodimethane (TCNQ) and2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

a metal oxide, such as tungsten oxide or molybdenum oxide;

1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221,

but embodiments of the present disclosure are not limited thereto:

In Formula 221,

R₂₂₁ to R₂₂₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, wherein at least oneselected from R₂₂₁ to R₂₂₃ may have at least one substituent selectedfrom a cyano group, —F, —Cl, —Br, —I, a C₁-C₂ alkyl group substitutedwith —F, a C₁-C₂₀ alkyl group substituted with —Cl, a C₁-C₂₀ alkyl groupsubstituted with —Br, and a C₁-C₂₀ alkyl group substituted with —I.

[Emission Layer in Organic Layer 150]

When the organic light-emitting device 10 is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, or a blue emission layer,according to a sub-pixel. In one or more embodiments, the emission layermay have a stacked structure of two or more layers selected from a redemission layer, a green emission layer, and a blue emission layer, inwhich the two or more layers contact each other or are separated fromeach other. In one or more embodiments, the emission layer may includetwo or more materials selected from a red light-emitting material, agreen light-emitting material, and a blue light-emitting material, inwhich the two or more materials are mixed with each other in a singlelayer to emit white light.

The emission layer may include a fluorescence emitter having TTAcharacteristics, and the arylamine compound may be included in thefluorescence emitter having TTA characteristics.

The emission layer may include a host and a dopant. The dopant mayinclude a fluorescence emitter having TTA characteristics, and thearylamine compound may be included in the fluorescence emitter havingTTA characteristics.

In the emission layer, an amount of the dopant may be in a range ofabout 0.01 parts by weight to about 15 parts by weight based on 100parts by weight of the host, but embodiments of the present disclosureare not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within this range, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

[Host in Emission Layer]

The host may include a compound represented by Formula 301:

[Ar₃₀₁]_(xb11)-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb21)  <Formula 301>

In Formula 301,

Ar₃₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xb11 may be 1, 2, or 3,

L₃₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xb1 may be an integer from 0 to 5,

R₃₀₁ may be selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂),—B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), and —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5, and

Q₃₀₁ to Q₃₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group, but embodiments of the presentdisclosure are not limited thereto.

In one embodiment Ar₃₀₁ in Formula 301 may be selected from:

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup; and

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group, but embodiments of the present disclosureare not limited thereto.

When xb11 in Formula 301 is 2 or more, two or more Ar₃₀₁(s) may belinked via a single bond.

In one or more embodiments, the compound represented by Formula 301 maybe represented by Formula 301-1 or 301-2:

In Formulae 301-1 and 301-2,

ring A₃₀₁ to ring A₃₀₄ may each independently be selected from a benzenering, a naphthalene ring, a phenanthrene ring, a fluoranthene ring, atriphenylene ring, a pyrene ring, a chrysene ring, a pyridine ring, apyrimidine ring, an indene ring, a fluorene ring, a spiro-bifluorenering, a benzofluorene ring, a dibenzofluorene ring, an indole ring, acarbazole ring, a benzocarbazole ring, a dibenzocarbazole ring, a furanring, a benzofuran ring, a dibenzofuran ring, a naphthofuran ring, abenzonaphthofuran ring, a dinaphthofuran ring, a thiophene ring, abenzothiophene ring, a dibenzothiophene ring, a naphthothiophene ring, abenzonaphthothiophene ring, and a dinaphthothiophene ring,

X₃₀₁ may be O, S, or N-[(L₃₀₄)_(xb4)-R₃₀₄],

R₃₁₁ to R₃₁₄ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═)(Q₃₁)(Q₃₂),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, R₃₀₁, and Q₃₁ to Q₃₃ are the same as described above,

L₃₀₂ to L₃₀₄ may each independently be the same as defined in connectionwith L₃₀₁

xb2 to xb4 may each independently be the same as defined in connectionwith xb1, and

R₃₀₂ to R₃₀₄ may each independently be the same as defined in connectionwith R₃₀₁.

For example, in Formulae 301, 301-1, and 301-2, L₃₀₁ to L₃₀₄ may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described above.

In one embodiment, R₃₀₁ to R₃₀₄ in Formulae 301, 301-1, and 301-2 mayeach independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described above.

In one embodiment, the host may include an alkaline earth-metal complex.For example, the host may be selected from a Be complex (for example,Compound H55), a Mg complex, and a Zn complex.

In one or more embodiments, the host may include at least one selectedfrom 9,10-di(2-naphthyl)anthracene (ADN),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene(mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55,but embodiments of the present disclosure are not limited thereto:

[Phosphorescent Dopant Included in Emission Layer of Organic Layer 150]

The emission layer may include a phosphorescent dopant further. Thephosphorescent dopant may include the organometallic compoundrepresented by Formula 1.

In addition, the phosphorescent dopant may include an organometalliccomplex represented by Formula 401:

In Formulae 401 and 402,

M may be selected from iridium (Ir), platinum (Pt), palladium (Pd),osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu),terbium (Tb), rhodium (Rh), and thulium (Tm),

L₄₀₁ may be a ligand represented by Formula 402, and xc1 may be 1, 2, or3, wherein, when xc1 is 2 or more, two or more L₄₀₁(s) may be identicalto or different from each other,

L₄₀₂ may be an organic ligand, and xc2 may be an integer from 0 to 4,wherein, when xc2 is 2 or more, two or more L₄₀₂(s) may be identical toor different from each other,

X₄₀₁ to X₄₀₄ may each independently be nitrogen or carbon,

X₄₀₁ and X₄₀₃ may be linked via a single bond or a double bond, and X₄₀₂and X₄₀₄ may be linked via a single bond or a double bond,

ring A₄₀₁ and ring A₄₀₂ may each independently be a C₅-C₆₀ carbocyclicgroup or a C₁-C₆₀ heterocyclic group,

X₄₀₅ may be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)-*′,*—C(Q₄₁₁)(Q₄₁₁)-*′, *—C(Q₄₁₁)=C(Q₄₁₂)-*′, *—C(Q₄₁₁)=*′, or *═C═*′,wherein Q₄₁₁ and Q₄₁₂ may each independently be hydrogen, deuterium, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenylgroup, a terphenyl group, or a naphthyl group,

X₄₀₆ may be a single bond, 0, or S,

R₄₀₁ and R₄₀₂ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₁-C₂₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃),—N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), and—P(═O)(Q₄₀₁)(Q₄₂), wherein Q₄₀₁ to Q₄₀₃ may each independently beselected from C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₆-C₂₀ arylgroup, and a C₁-C₂₀ heteroaryl group,

xc11 and xc12 may each independently be an integer from 0 to 10, and

* and *′ in Formula 402 each indicate a binding site to M′ in Formula401.

In one embodiment, ring A₄₀₁ and ring A₄₀₂ in Formula 402 may eachindependently be selected from a benzene group, a naphthalene group, afluorene group, a spiro-bifluorene group, an indene group, a pyrrolegroup, a thiophene group, a furan group, an imidazole group, a pyrazolegroup, a thiazole group, an isothiazole group, an oxazole group, anisoxazole group, a pyridine group, a pyrazine group, a pyrimidine group,a pyridazine group, a quinoline group, an isoquinoline group, abenzoquinoline group, a quinoxaline group, a quinazoline group, acarbazole group, a benzimidazole group, a benzofuran group, abenzothiophene group, an isobenzothiophene group, a benzoxazole group,an isobenzoxazole group, a triazole group, a tetrazole group, anoxadiazole group, a triazine group, a dibenzofuran group, and adibenzothiophene group.

In one or more embodiments, in Formula 402, i) X₄₀₁ may be nitrogen, andX₄₀₂ may be carbon, or ii) X₄₀₁ and X₄₀₂ may each be nitrogen at thesame time.

In one or more embodiments, R₄₀₁ and R₄₀₂ in Formula 402 may eachindependently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a phenyl group, a naphthyl group, a cyclopentyl group,a cyclohexyl group, an adamantanyl group, a norbornanyl group, and anorbornenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group a phenyl group, a biphenyl group,a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

—Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₂), —C(═O)(Q₄₀₁),—S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂), and

Q₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, and anaphthyl group, but embodiments of the present disclosure are notlimited thereto.

In one or more embodiments, in Formula 401, when xc1 is 2 or more, twoA₄₀₁(s) in two or more L₄₀₁(s) may optionally be linked via X₄₀₇, whichis a linking group, or when xc2 is 2 or more, two A₄₀₂(s) in two or moreL₄₀₁(s) may optionally be linked via X₄₀₈, which is a linking group (seeCompounds PD1 to PD4 and PD7). X₄₀₇ and X₄₀₈ may each independently be asingle bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₃)-*′,*—C(Q₄₁₃)(Q₄₁₄)-*′, or *—C(Q₄₁₃)=C(Q₄₁₄)-*′ (wherein Q₄₁₃ and Q₄₁₄ mayeach independently be hydrogen, deuterium, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, or a naphthyl group), but embodiments of the present disclosureare not limited thereto.

L₄₀₂ in Formula 401 may be a monovalent, divalent, or trivalent organicligand. For example, L402 may be halogen, diketone (for example,acetylacetonate), carboxylic acid (for example, picolinate), —C(═O),isonitrile, —CN, and a phosphorus-containing material (for example,phosphine or phosphite), but embodiments of the present disclosure arenot limited thereto.

In one embodiment, the phosphorescent dopant may be, for example,selected from Compounds PD1 to PD25, but embodiments of the presentdisclosure are not limited thereto:

[Fluorescent Dopant in Emission Layer]

The fluorescent dopant may include the compound represented by Formula1.

The fluorescent dopant may include an arylamine compound or astyrylaminecompound further.

The fluorescent dopant may include a compound represented by Formula 501

In Formula 501,

Ar₅₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

L₅₀₁ to L₅₀₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group

xd1 to xd3 may each independently be an integer from 0 to 3,

R₅₀₁ and R₅₀₂ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,and

xd4 may be an integer from 1 to 6.

In one embodiment, Ar₅₀₁ in Formula 501 may be selected from:

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup; and

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, L₅₀₁ to L₅₀₃ in Formula 501 may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group.

In one or more embodiments, R₅₀₁ and R₅₀₂ in Formula 501 may eachindependently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xd4 in Formula 501 may be 2, but embodimentsof the present disclosure are not limited thereto.

For example, the fluorescent dopant may be selected from Compounds FD1to FD22:

In one or more embodiments, the fluorescent dopant may be selected fromthe following compounds, but embodiments of the present disclosure arenot limited thereto:

[Electron Transport Region in Organic Layer 150]

The electron transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron transport region may include at least one selected from abuffer layer, a hole blocking layer, an electron control layer, anelectron transport layer, and an electron injection layer, butembodiments of the present disclosure are not limited thereto.

For example, the electron transport region may have an electrontransport layer/electron injection layer structure, a hole blockinglayer/electron transport layer/electron injection layer structure, anelectron control layer/electron transport layer/electron injection layerstructure, or a buffer layer/electron transport layer/electron injectionlayer structure, wherein for each structure, constituting layers aresequentially stacked from an emission layer. However, embodiments of thestructure of the electron transport region are not limited thereto.

The electron transport region (for example, a buffer layer, a holeblocking layer, an electron control layer, or an electron transportlayer in the electron transport region) may include a metal-freecompound containing at least one 7 electron-depleted nitrogen-containingring.

The “π electron-depleted nitrogen-containing ring” indicates a C₁-C₆₀heterocyclic group having at least one *—N═*′ moiety as a ring-formingmoiety.

For example, the “π electron-depleted nitrogen-containing ring” may bei) a 5-membered to 7-membered heteromonocyclic group having at least one*—N═*′ moiety, ii) a heteropolycyclic group in which two or more5-membered to 7-membered heteromonocyclic groups each having at leastone *—N═*′ moiety are condensed with each other, or iii) aheteropolycyclic group in which at least one of 5-membered to 7-memberedheteromonocyclic groups, each having at least one *—N═*′ moiety, iscondensed with at least one C₅-C₆₀ carbocyclic group.

Examples of the 7 electron-depleted nitrogen-containing ring include animidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, anisoxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, anindazole, a purine, a quinoline, an isoquinoline, a benzoquinoline, aphthalazine, a naphthyridine, a quinoxaline, a quinazoline, a cinnoline,a phenanthridine, an acridine, a phenanthroline, a phenazine, abenzimidazole, an isobenzothiazole, a benzoxazole, an isobenzoxazole, atriazole, a tetrazole, an oxadiazole, a triazine, a thiadiazole, animidazopyridine, an imidazopyrimidine, and an azacarbazole, but are notlimited thereto.

For example, the electron transport region may include a compoundrepresented by Formula 601:

[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe1)-R₆₀₁]_(xe21)  <Formula 601>

In Formula 601,

Ar₆₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xe11 may be 1, 2, or 3,

L₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xe1 may be an integer from 0 to 5,

R₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁),—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁ to Q₆₀₃ may each independently be a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or anaphthyl group, and

xe21 may be an integer from 1 to 5.

In one embodiment, at least one of Ar₆₀₁(s) in the number of xe11 andR₆₀₁(s) in the number of xe21 may include the 7 electron-depletednitrogen-containing ring.

In one embodiment, Ar₆₀₁ in Formula 601 may be selected from:

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group; and

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

When xe11 in Formula 601 is 2 or more, two or more Ar₆₀₁(s) may belinked via a single bond.

In one or more embodiments, Ar₆₀₁ in Formula 601 may be an anthracenegroup.

In one or more embodiments, the compound represented by Formula 601 maybe represented by Formula 601-1:

In Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), and X₆₁₆ may be N orC(R₆₁₆), wherein at least one selected from X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ may each independently be the same as defined in connectionwith L₆₀₁,

xe₆₁₁ to xe₆₁₃ may each independently be the same as defined inconnection with xe1,

R₆₁₁ to R₆₁₃ may each independently be the same as defined in connectionwith R₆₀₁, and

R₆₁₄ to R₆₁₆ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

In one embodiment, L₆₀₁ and L₆₁₁ to L₆₁₃ in Formulae 601 and 601-1 mayeach independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, and an azacarbazolyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and601-1 may each independently be 0, 1, or 2.

In one or more embodiments, R₆₀₁ and R₆₁₁ to R₆₁₃ in Formulae 601 and601-1 may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

—S(═O)₂(Q₆₀₁) and —P(═O)(Q₆₀₁)(Q₆₀₂), and

Q₆₀₁ and Q₆₀₂ are the same as described above.

The electron transport region may include at least one compound selectedfrom Compounds ET1 to ET36, but embodiments of the present disclosureare not limited thereto:

In one or more embodiments, the electron transport region may include atleast one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline(BCP), 4,7-dphenyl-1,10-phenanthroline (Bphen), Alq₃, BAlq,3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), and NTAZ:

A thickness of the buffer layer, the hole blocking layer, or theelectron control layer may be in a range of about 20 Å to about 1,000 Å,for example, about 30 Å to about 300 Å. When the thicknesses of thebuffer layer, the hole blocking layer, and the electron control layerare within these ranges, the electron transport region may haveexcellent hole blocking characteristics or electron controlcharacteristics without a substantial increase in driving voltage.

A thickness of the electron transport layer may be from about 100 Å toabout 1,000 Å, for example, about 150 Å to about 500 Å. When thethickness of the electron transport layer is within the range describedabove, satisfactory electron transport characteristics may be obtainedwithout a substantial increase in driving voltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include at least one selected fromalkali metal complex and alkaline earth-metal complex. The alkali metalcomplex may include a metal ion selected from a Li ion, a Na ion, a Kion, a Rb ion, and a Cs ion, and the alkaline earth-metal complex mayinclude a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Srion, and a Ba ion. A ligand coordinated with the metal ion of the alkalimetal complex or the alkaline earth-metal complex may be selected from ahydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, ahydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyl oxazole, ahydroxy phenylthiazole, a hydroxy diphenyl oxadiazole, a hydroxydiphenylthiadiazole, a hydroxy phenylpyridine, a hydroxyphenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, aphenanthroline, and a cyclopentadiene, but embodiments of the presentdisclosure are not limited thereto.

For example, the metal-containing material may include a Li complex. TheLi complex may include, for example, Compound ET-D1 (lithium quinolate,LiQ) or ET-D2:

The electron transport region may include an electron injection layerthat facilitates electron injection from the second electrode 190. Theelectron injection layer may directly contact the second electrode 190.

The electron injection layer may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron injection layer may include an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof.

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In oneembodiment, the alkali metal may be Li, Na, or Cs. In one or moreembodiments, the alkali metal may be Li or Cs, but embodiments of thepresent disclosure are not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

The alkali metal compound, the alkaline earth-metal compound, and therare earth metal compound may be selected from oxides and halides (forexample, fluorides, chlorides, bromides, or iodides) of the alkalimetal, the alkaline earth-metal, and the rare earth metal.

The alkali metal compound may be selected from alkali metal oxides, suchas Li₂O, Cs₂O, or K₂O, and alkali metal halides, such as LiF, NaF, CsF,KF, LiI, NaI, CsI, or KI. In one embodiment, the alkali metal compoundmay be selected from LiF, Li₂O, NaF, LiI, NaI, CsI, and KI, butembodiments of the present disclosure are not limited thereto.

The alkaline earth-metal compound may be selected from alkalineearth-metal oxides, such as BaO, SrO, CaO, Ba_(x)Sr_(1-x)O (0<x<1), orBa_(x)Ca_(1-x)O (0<x<1). In one embodiment, the alkaline earth-metalcompound may be selected from BaO, SrO, and CaO, but embodiments of thepresent disclosure are not limited thereto.

The rare earth metal compound may be selected from YbF₃, ScF₃, Sc₂O₃,Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In one embodiment, the rare earth metalcompound may be selected from YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, and TbI₃,but embodiments of the present disclosure are not limited thereto.

The alkali metal complex, the alkaline earth-metal complex, and the rareearth metal complex may include an ion of alkali metal, alkalineearth-metal, and rare earth metal as described above, and a ligandcoordinated with a metal ion of the alkali metal complex, the alkalineearth-metal complex, or the rare earth metal complex may be selectedfrom hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline,hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxyphenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole,hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene,but embodiments of the present disclosure are not limited thereto.

The electron injection layer may consist of an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof, as described above. In one or moreembodiments, the electron injection layer may further include an organicmaterial. When the electron injection layer further includes an organicmaterial, an alkali metal, an alkaline earth metal, a rare earth metal,an alkali metal compound, an alkaline earth-metal compound, a rare earthmetal compound, an alkali metal complex, an alkaline earth-metalcomplex, a rare earth metal complex, or any combinations thereof may behomogeneously or non-homogeneously dispersed in a matrix including theorganic material.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. When a thicknessof the electron injection layer is within these ranges, satisfactoryelectron injection characteristics may be obtained without substantialincrease in driving voltage.

[Second Electrode 190]

The second electrode 190 may be disposed on the organic layer 150 havingsuch a structure. The second electrode 190 may be a cathode which is anelectron injection electrode, and in this regard, a material for formingthe second electrode 190 may be selected from metal, an alloy, anelectrically conductive compound, and a combination thereof, which havea relatively low work function.

The second electrode 190 may include at least one selected from lithium(Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are notlimited thereto. The second electrode 190 may be a transmissiveelectrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single-layered structure, or amulti-layered structure including two or more layers.

[Description of FIGS. 2 to 4]

FIG. 2 is a schematic view of an organic light-emitting device 20according to an embodiment. The organic light-emitting device 20includes a first capping layer 210, the first electrode 110, the organiclayer 150, and the second electrode 190, which are sequentially stackedin this stated order. FIG. 3 is a schematic view of an organiclight-emitting device 30 according to an embodiment. The organiclight-emitting device 30 includes the first electrode 110, the organiclayer 150, the second electrode 190, and a second capping layer 220,which are sequentially stacked in this stated order. FIG. 4 is aschematic view of an organic light-emitting device 40 according to anembodiment. The organic light-emitting device 40 includes the firstcapping layer 210, the first electrode 110, the organic layer 150, thesecond electrode 190, and the second capping layer 220, which aresequentially stacked in this stated order.

Regarding FIGS. 2, 3, and 4, the first electrode 110, the organic layer150, and the second electrode 190 may be understood by referring to thedescription presented in connection with FIG. 1.

In the organic layer 150 of each of the organic light-emitting devices20 and 40, light generated in an emission layer may pass through thefirst electrode 110 and the first capping layer 210 toward the outside,wherein the first electrode 110 may be a semi-transmissive electrode ora transmissive electrode. In the organic layer 150 of each of theorganic light-emitting devices 30 and 40, light generated in an emissionlayer may pass through the second electrode 190 and the second cappinglayer 220 toward the outside, wherein the second electrode 190 may be asemi-transmissive electrode or a transmissive electrode.

The first capping layer 210 and the second capping layer 220 mayincrease external luminescence efficiency according to the principle ofconstructive interference.

The first capping layer 210 and the second capping layer 220 may eachindependently be an organic capping layer including an organic material,an inorganic capping layer including an inorganic material, or acomposite capping layer including an organic material and an inorganicmaterial.

At least one selected from the first capping layer 210 and the secondcapping layer 220 may each independently include at least one materialselected from carbocyclic compounds, heterocyclic compounds, amine-basedcompounds, porphyrine derivatives, phthalocyanine derivatives,naphthalocyanine derivatives, alkali metal complexes, and alkalineearth-based complexes. The carbocyclic compound, the heterocycliccompound, and the amine-based compound may be optionally substitutedwith a substituent containing at least one element selected from O, N,S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selectedfrom the first capping layer 210 and the second capping layer 220 mayeach independently include an amine-based compound.

In one embodiment, at least one selected from the first capping layer210 and the second capping layer 220 may each independently include thecompound represented by Formula 201 or the compound represented byFormula 202.

In one or more embodiments, at least one selected from the first cappinglayer 210 and the second capping layer 220 may each independentlyinclude a compound selected from Compounds HT28 to HT33 and CompoundsCP1 to CP5, but embodiments of the present disclosure are not limitedthereto:

Hereinbefore, the organic light-emitting device according to anembodiment has been described in connection with FIGS. 1 to 4, butembodiments of the present disclosure are not limited thereto.

Layers constituting the hole transport region, an emission layer, andlayers constituting the electron transport region may be formed in acertain region by using one or more suitable methods selected fromvacuum deposition, spin coating, casting, Langmuir-Blodgett (LB)deposition, ink-jet printing, laser-printing, and laser-induced thermalimaging (LITI).

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed byvacuum deposition, the deposition may be performed at a depositiontemperature of about 100° C. to about 500° C., a vacuum degree of about10⁻⁸ torr to about 10⁻³ torr, and a deposition speed of about 0.01 Å/secto about 100 Å/sec by taking into account a material to be included in alayer to be formed, and the structure of a layer to be formed.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed by spincoating, the spin coating may be performed at a coating speed of about2,000 rpm to about 5,000 rpm and at a heat treatment temperature ofabout 80° C. to about 200° C. by taking into account a material to beincluded in a layer to be formed, and the structure of a layer to beformed.

[Apparatus]

The organic light-emitting device may be included in variousapparatuses. For example, a light-emitting apparatus, an authenticationapparatus, or an electronic apparatus, which includes the organiclight-emitting device, may be provided.

The light-emitting apparatus may further include, in addition to theorganic light-emitting device, a thin-film transistor including a sourceelectrode and a drain electrode. One of the source electrode and thedrain electrode of the thin-film transistor may be electricallyconnected to one of the first electrode and the second electrode of theorganic light-emitting device. The light-emitting apparatus may be usedas various displays, light sources, and the like.

The authentication apparatus may be, for example, a biometricauthentication apparatus for authenticating an individual by usingbiometric information of a biometric body (for example, a fingertip, apupil, or the like).

The authentication apparatus may further include, in addition to theorganic light-emitting device, a biometric information collector.

The electronic apparatus may be applied to personal computers (forexample, a mobile personal computer), mobile phones, digital cameras,electronic organizers, electronic dictionaries, electronic gamemachines, medical instruments (for example, electronic thermometers,sphygmomanometers, blood glucose meters, pulse measurement devices,pulse wave measurement devices, electrocardiogram (ECG) displays,ultrasonic diagnostic devices, or endoscope displays), fish finders,various measuring instruments, meters (for example, meters for avehicle, an aircraft, and a vessel), projectors, and the like, butembodiments of the present disclosure are not limited thereto.

[General Definition of Substituents]

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched aliphatic saturated hydrocarbon monovalent group having 1 to 60carbon atoms, and examples thereof include a methyl group, an ethylgroup, a propyl group, an isobutyl group, a sec-butyl group, atert-butyl group, a pentyl group, an isoamyl group, and a hexyl group.The term “C₁-C₆₀ alkylene group” as used herein refers to a divalentgroup having the same structure as the C₁-C₆₀ alkyl group.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a hydrocarbongroup having at least one carbon-carbon double bond in the middle or atthe terminus of the C₂-C₆₀ alkyl group, and examples thereof include anethenyl group, a propenyl group, and a butenyl group. The term “C₂-C₆₀alkenylene group” as used herein refers to a divalent group having thesame structure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a hydrocarbongroup having at least one carbon-carbon triple bond in the middle or atthe terminus of the C₂-C₆₀ alkyl group, and examples thereof include anethynyl group, and a propynyl group. The term “C₂-C₆₀ alkynylene group”as used herein refers to a divalent group having the same structure asthe C₂-C₆₀ alkynyl group.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and examples thereof include a methoxy group, an ethoxy group, and anisopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, andexamples thereof include a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term“C₃-C₁₀ cycloalkylene group” as used herein refers to a divalent grouphaving the same structure as the C₃-C₁₀ cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein refers to amonovalent monocyclic group having at least one heteroatom selected fromN, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, andexamples thereof include a 1,2,3,4-oxatriazolidinyl group, atetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term“C₁-C₁₀ heterocycloalkylene group” as used herein refers to a divalentgroup having the same structure as the C₁-C₁₀ heterocycloalkyl group.

The term C₃-C₁₀ cycloalkenyl group used herein refers to a monovalentmonocyclic group that has 3 to 10 carbon atoms and at least onecarbon-carbon double bond in the ring thereof and no aromaticity, andexamples thereof include a cyclopentenyl group, a cyclohexenyl group,and a cycloheptenyl group. The term “C₃-C₁₁ cycloalkenylene group” asused herein refers to a divalent group having the same structure as theC₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms,and at least one carbon-carbon double bond in its ring. Non-limitingexamples of the C₁-C₁₀ heterocycloalkenyl group include a4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, anda 2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup” as used herein refers to a divalent group having the samestructure as the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having 6 to 60 carbon atoms, and aC₆-C₆₀ arylene group used herein refers to a divalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. Non-limitingexamples of the C₆-C₆₀ aryl group include a phenyl group, a naphthylgroup, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, anda chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylenegroup each include two or more rings, the rings may be fused to eachother.

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalentgroup having a carbocyclic aromatic system that has at least oneheteroatom selected from N, O, Si, P, and S as a ring-forming atom, inaddition to 1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylene group”as used herein refers to a divalent group having a carbocyclic aromaticsystem that has at least one heteroatom selected from N, O, Si, P, and Sas a ring-forming atom, in addition to 1 to 60 carbon atoms.Non-limiting examples of the C₁-C₆₀ heteroaryl group include a pyridinylgroup, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, and an isoquinolinyl group. Whenthe C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylene group eachinclude two or more rings, the rings may be condensed with each other.

The term “C₆-C₆₀ aryloxy group” as used herein refers to —OA₁₀₂ (whereinA₁₀₂ is the C₆-C₆₀ aryl group), and the term “C₆-C₆₀ arylthio group” asused herein indicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

The term “C₁-C₆₀ heteroaryloxy group” as used herein refers to —OA₁₀₄(wherein A₁₀₄ is the C₁-C₆₀ heteroaryl group), and the term “C₁-C₆₀heteroarylthio group” as used herein refers to —SA₁₀₅ (wherein A₁₀₅ isthe C₁-C₆₀ heteroaryl group).

The term “monovalent non-aromatic condensed polycyclic group” as usedherein refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed with each other, only carbonatoms as ring-forming atoms, and no aromaticity in its entire molecularstructure. A detailed example of the monovalent non-aromatic condensedpolycyclic group is a fluorenyl group. The term “divalent non-aromaticcondensed polycyclic group” as used herein refers to a divalent grouphaving the same structure as the monovalent non-aromatic condensedpolycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein refers to a monovalent group (for example, having 1 to 60carbon atoms) having two or more rings condensed to each other, at leastone heteroatom selected from N, O, Si, P, and S, other than carbonatoms, as a ring-forming atom, and no aromaticity in its entiremolecular structure. An example of the monovalent non-aromatic condensedheteropolycyclic group is a carbazolyl group. The term “divalentnon-aromatic condensed heteropolycyclic group” as used herein refers toa divalent group having the same structure as the monovalentnon-aromatic condensed heteropolycyclic group.

The term “C₅-C₆₀ carbocyclic group” as used herein refers to amonocyclic or polycyclic group having 5 to 60 carbon atoms in which aring-forming atom is a carbon atom only. The term “C₅-C₆₀ carbocyclicgroup” as used herein refers to an aromatic carbocyclic group or anon-aromatic carbocyclic group. The C₅-C₆₀ carbocyclic group may be aring, such as benzene, a monovalent group, such as a phenyl group, or adivalent group, such as a phenylene group. In one or more embodiments,depending on the number of substituents connected to the C₅-C₆₀carbocyclic group, the C₅-C₆₀ carbocyclic group may be a trivalent groupor a quadrivalent group.

The term “C₁-C₆₀ heterocyclic group” as used herein refers to a grouphaving the same structure as the C₄-C₆₀ carbocyclic group, except thatas a ring-forming atom, at least one heteroatom selected from N, O, Si,P, and S is used in addition to carbon (the number of carbon atoms maybe in a range of 1 to 60).

In the present specification, at least one substituent of thesubstituted C₅-C₆₀ carbocyclic group, the substituted C₁-C₆₀heterocyclic group, the substituted C₃-C₁₀ cycloalkylene group, thesubstituted C₁-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀ heterocycloalkenylenegroup, the substituted C₆-C₆₀ arylene group, the substituted C₁-C₆₀heteroarylene group, the substituted divalent non-aromatic condensedpolycyclic group, the substituted divalent non-aromatic condensedheteropolycyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted C₁-C₆₀heteroaryloxy group, thesubstituted C₁-C₆₀heteroarylthio group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

The term “Ph” as used herein refers to a phenyl group, the term “Me” asused herein refers to a methyl group, the term “Et” as used hereinrefers to an ethyl group, the term “ter-Bu” or “Bu^(t)” as used hereinrefers to a tert-butyl group, and the term “OMe” as used herein refersto a methoxy group.

The term “biphenyl group” as used herein refers to “a phenyl groupsubstituted with a phenyl group”. In other words, the “biphenyl group”is a substituted phenyl group having a C₆-C₆₀ aryl group as asubstituent.

The term “terphenyl group” as used herein refers to “a phenyl groupsubstituted with a biphenyl group”. In other words, the “terphenylgroup” is a phenyl group having, as a substituent, a C₆-C₆₀ aryl groupsubstituted with a C₆-C₆₀ aryl group.

*, *′, and *″ as used herein, unless defined otherwise, each refer to abinding site to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments and an organiclight-emitting device according to embodiments will be described indetail with reference to Synthesis Examples and Examples. The wording “Bwas used instead of A” used in describing Synthesis Examples refers tothat an identical molar equivalent of B was used in place of A.

EXAMPLES Synthesis Examples Synthesis Example 1: Synthesis of Compound 1

N,N-diphenyl-[1,1′-biphenyl]-2-amine (Compound 1-1) (32 g, 0.10 mol) wasstirred and dissolved in 50 mL of dimethylformamide (DMF) at roomtemperature, and the solution was cooled to a temperature of 0° C.N-bromosuccinimide (2.0 g, 0.11 mol) dissolved in DMF was slowly addedto the solution and stirred for 3 hours. The reaction solution washeated to room temperature, and water was added to the reaction solutionto quench the reaction. Then, the eluted solid was filtered underreduced pressure and recrystallized in ethanol to obtain5-bromo-N,N-diphenyl-[1,1′-biphenyl]-2-amine (Compound 1-2) (28 g, 70mmol).

5-bromo-N,N-diphenyl-[1,1′-biphenyl]-2-amine (Compound 1-2) (28 g, 70mmol), K₂CO₃ (14 g, 0.10 mol), Pd(PPh₃)₄ (4.1 g, 3.5 mmol), and9,9′-spirobi[fluorene]-2-ylboronic acid (Compound 1-3) (25 g, 69 mmol)were dried in a vacuum and dissolved in DMF (150 mL)/anhydrous EtOH (150mL). The reaction solution was nitrogen-bubbled for 20 minutes andstirred at a temperature of 80° C. for 24 hours. Then, the reactionsolution was cooled to room temperature, and a solvent was removed fromthe reaction solution under reduced pressure and washed with an excessof hexane and water. An organic layer was separated therefrom, dried byusing MgSO₄, and then concentrated under reduced pressure. A productobtained therefrom was purified by column chromatography usingdichloromethane/hexane (1:1, v/v) to obtain5-(9,9′-spirobi[fluorene]-2-yl)-N,N-diphenyl-[1,1′-biphenyl]-2-amine(Compound 1) (31 g, 48 mmol) (yield: 69%).

Synthesis Example 2: Synthesis of Compound 2

30 mL of toluene was added to 4-bromo-2-amino-1,1′-biphenyl (Compound2-1) (5.0 g, 20 mmol), iodobenzene (Compound 2-2) (10 g, 49 mmol), KOH(5.9 g, 0.15 mol), 1,10-phenanthroline (0.15 g), and CuCl (0.10 g), andthe reaction mixture was stirred for 15 hours under reflux. The reactionmixture was cooled to room temperature and diluted with 200 mL oftoluene. The toluene solution was washed with distilled water,separated, and then dried by using MgSO₄, and a solvent was removedtherefrom under reduced pressure. The eluted solid was recrystallized inhexane/toluene (4:1, v/v) to obtain4-bromo-N,N-diphenyl-[1,1′-biphenyl]-2-amine (Compound 2-3) (3.2 g, 8.0mmol). 4-bromo-N,N-diphenyl-[1,1′-biphenyl]-2-amine (Compound 2-3) (3.2g, 8.0 mmol), K₂CO₃ (2.1 g, 15 mol), Pd(PPh₃)₄ (1.2 g, 1.0 mmol), and9,9′-spirobi[fluorene]-2-ylboronic acid (Compound 2-4) (2.9 g, 8.0 mmol)were dried in a vacuum and dissolved in DMA (100 mL)/anhydrous EtOH (30mL). The reaction solution was nitrogen-bubbled for 20 minutes andstirred at a temperature of 100° C. for 24 hours. Then, the reactionsolution was cooled to room temperature, and a solvent was removed fromthe reaction solution under reduced pressure and washed with an excessof hexane and water. An organic layer was separated therefrom, dried byusing MgSO₄, and then concentrated under reduced pressure. A productobtained therefrom was purified by column chromatography usingdichloromethane (DCM) to obtain4-(9,9′-spirobi[fluorene]-2-yl)-N,N-diphenyl-[1,1′-biphenyl]-2-amine(Compound 2) (3.7 g, 5.8 mmol) (yield: 73%).

Synthesis Example 3: Synthesis of Compound 3

N-phenyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-[1,1′-biphenyl]-2-amine(Compound 3-1) (4.5 g, 10 mmol), K₂CO₃ (2.1 g, 15 mol), Pd(PPh₃)₄ (1.8g, 1.5 mmol), and 2-bromo-9,9′-spirobi[fluorene] (Compound 3-2) (4.0 g,10 mmol) were dried in a vacuum and dissolved in 1,4-dioxane (60mL)/anhydrous EtOH (15 mL). The reaction solution was nitrogen-bubbledfor 20 minutes and stirred at a temperature of 100° C. for 24 hours.Then, the reaction solution was cooled to room temperature, and asolvent was removed from the reaction solution under reduced pressureand washed with an excess of DCM. An organic layer was separatedtherefrom, dried by using MgSO₄, and then concentrated under reducedpressure. A product obtained therefrom was purified by columnchromatography using DCM to obtainN-(3-(9,9′-spirobi[fluorene]-2-yl)phenyl)-N-phenyl-[1,1′-biphenyl]-2-amine(Compound 3) (4.3 g, 6.7 mmol) (yield: 67%).

Synthesis Example 4: Synthesis of Compound 4

N-phenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-[1,1′-biphenyl]-2-amine(Compound 4-1) (4.5 g, 10 mmol), K₂CO₃ (2.1 g, 15 mol), Pd(PPh₃)₄ (1.8g, 1.5 mmol), and 2-bromo-9,9′-spirobi[fluorene] (Compound 4-2) (4.0 g,10 mmol) were dried in a vacuum and dissolved in 1,4-dioxane (60mL)/anhydrous EtOH (15 mL). The reaction solution was nitrogen-bubbledfor 20 minutes and stirred at a temperature of 100° C. for 24 hours.Then, the reaction solution was cooled to room temperature, and asolvent was removed from the reaction solution under reduced pressureand washed with an excess of DCM. An organic layer was separatedtherefrom, dried by using MgSO₄, and then concentrated under reducedpressure. A product obtained therefrom was purified by columnchromatography using DCM to obtainN-(4-(9,9′-spirobi[fluorene]-2-yl)phenyl)-N-phenyl-[1,1′-biphenyl]-2-amine(Compound 4) (4.8 g, 7.5 mmol) (yield: 75%).

¹H NMR of each of Compounds synthesized in Synthesis Examples 1 to 4 isshown in Table 1.

Synthesis methods of compounds other than Compounds shown in Table 1 mayalso be easily recognized by those of ordinary skill in the art byreferring to the synthesis mechanisms and source materials describedabove.

TABLE 1 Compound ¹H NMR (d₅-DMSO, 500 MHz) 1 δ 8.09 (1H), 7.90-7.89(5H), 7.78 (1H), 7.65 (1H), 7.59-7.55 (2H), 7.45-7.41 (5H), 7.38 (1H),7.28- 7.27 (5H), 7.24 (4H), 7.08 (6H), 7.00 (2H) ppm. 2 δ 8.09 (1H),7.92-7.89 (5H), 7.78 (1H), 7.55 (1H), 7.46-7.41 (6H), 7.38 (1H),7.28-7.27 (5H), 7.24 (4H), 7.08 (6H), 7.00 (2H), 6.91 (1H) ppm. 3 δ 8.10(2H), 7.91-7.89 (4H), 7.78 (1H), 7.55 (2H), 7.45-7.37 (8H), 7.29-7.27(6H), 7.24 (2H), 7.18- 7.17 (2H), 7.14 (1H), 7.08 (4H), 6.99 (1H) ppm. 4δ 8.10 (2H), 7.90-7.78 (5H), 7.55 (3H), 7.45-7.41 (5H), 7.39-7.37 (5H),7.29-7.27 (5H), 7.24 (2H), 7.14 (1H), 7.08 (4H), 7.00 (1H) ppm.

Example 1

A Corning (15 Ω/cm², 1,200 Å) ITO glass substrate was cut to a size of50 mm×50 mm×0.5 mm, sonicated with isopropyl alcohol and pure water eachfor 10 minutes, and then cleaned by exposure to ultraviolet rays andozone for 10 minutes. Then, the ITO glass substrate was provided to avacuum deposition apparatus.

NPB was vacuum-deposited on the ITO glass substrate to form a holeinjection layer having a thickness of 40 Å, and mCP was vacuum-depositedon the hole injection layer to form a hole transport layer having athickness of 10 Å. mCBP and Compound 1 were co-deposited on the holetransport layer at a weight ratio of 85:15 to form an emission layerhaving a thickness of 200 Å. Then, ET1 was vacuum-deposited on theemission layer to form an electron transport layer having a thickness of300 Å. Al was vacuum-deposited on the electron transport layer to forman Al electrode having a thickness of 1,200 Å, thereby completing themanufacture of an organic light-emitting device.

Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 2 was used instead of Compound 1 informing an emission layer.

Example 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 3 was used instead of Compound 1 informing an emission layer.

Example 4

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 4 was used instead of Compound 1 informing an emission layer.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound C-2 was used instead of Compound 1 informing an emission layer.

Comparative Example 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound C-3 was used instead of Compound 1 informing an emission layer.

Comparative Example 4

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound C-4 was used instead of Compound 1 informing an emission layer.

Evaluation Example

The driving voltage, current efficiency, and external quantum efficiencyof the organic light-emitting devices manufactured according to Examples1 to 4 and Comparative Examples 1 to 4 were measured at a currentdensity of 10 mA/cm2 by using a current-voltage meter (Keithley SMU 236)and a luminance meter (PR650), and results thereof are shown in Table 1.

TABLE 2 External Driving Current quantum A′-B Compound of voltagedensity efficiency distance emission layer (V) (cd/A/y) (%) (Å) Example1 mCBP/1 3.5 152 10.2 3.54 Example 2 mCBP/2 3.8 141 8.9 3.99 Example 3mCBP/3 4.1 128 7.5 4.38 Example 4 mCBP/4 4.3 108 6.9 4.73 ComparativemCBP/C-1 4.7 56 4.3 — Example 1 Comparative mCBP/C-2 4.2 112 7.1 4.53Example 2 Comparative mCBP/C-3 4.5 98 5.8 4.82 Example 3 ComparativemCBP/C-4 4.4 101 6.5 4.78 Example 4

In Table 1, an A′-B distance is a distance between substituentscorresponding to the A′ phenyl group and the B phenyl group in Formula1, and was calculated by using Material studio 2018 program.

From Table 1, it is confirmed that the organic light-emitting devices ofExamples 1 to 8, in which the compound according to one or moreembodiments is used in the emission layer, have a low driving voltageand improved current efficiency and external quantum efficiency, ascompared with those of the organic light-emitting devices of ComparativeExamples 1 to 4.

The organic light-emitting device including the arylamine compound mayhave a low driving voltage, high efficiency, and along lifespan.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments.

Although certain exemplary embodiments and implementations have beendescribed herein, other embodiments and modifications will be apparentfrom this description. Accordingly, the inventive concepts are notlimited to such embodiments, but rather to the broader scope of theappended claims and various obvious modifications and equivalentarrangements as would be apparent to a person of ordinary skill in theart.

What is claimed is:
 1. An arylamine compound represented by Formula 1:

wherein, in Formula 1, R₁ to R₁₄ are each independently selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —C(═O)(Q₁),—N(Q₁)(Q₂), P(═O)(Q₁)(Q₂), and —S(═O)₂(Q₁)(Q₂), at least one substituentof the substituted C₅-C₆₀ carbocyclic group, the substituted C₁-C₆₀heterocyclic group, the substituted C₁-C₆₀ alkyl group, the substitutedC₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group, thesubstituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted C₁-C₆₀heteroaryloxy group, thesubstituted C₁-C₆₀heteroarylthio group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group is selected from:deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂),—B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic condensed heteropolycyclic group; a C₃-C₁₀ cycloalkylgroup, a C₁-C₁ heterocycloalkyl group, a C₃-C₁₁ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazino group, a hydrazonogroup, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂),—B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃,and Q₃₁ to Q₃₃ are each independently selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, a monovalent non-aromatic condensedheteropolycyclic group, a biphenyl group, and a terphenyl group, and adistance d between a center of an A′ phenyl group and a B phenyl groupis a distance by which orbitals of the A′ phenyl group and the B phenylgroup overlap each other.
 2. The arylamine compound of claim 1, whereinthe distance d is in a range of about 3 Å to about 5 Å.
 3. The arylaminecompound of claim 1, wherein at least one selected from R₂, R₃, R₆, andR₇ is a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, or a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.4. The arylamine compound of claim 1, wherein at least one selected fromR₂ and R₃ is a substituted or unsubstituted C₆-C₆₀ aryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, or a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group.
 5. The arylamine compoundof claim 1, wherein at least one selected from R₂, R₃, R₆, and R₇ isselected from a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, abiphenyl group, a terphenyl group, a pentalenyl group, an indenyl group,a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, apentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, an isoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, aquinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a dihydroacridinyl group, aphenanthrolinyl group, a phenazinyl group, a dihydrophenazinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, abenzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, atetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, atriazinyl group, a carbazolyl group, a dibenzofuranyl group, adibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolylgroup, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, anaphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranylgroup, a dinaphthothiophenyl group, a dinaphtho silolyl group, animidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinylgroup, a thiazolopyridinyl group, a benzonaphthyridinyl group, anazafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolylgroup, an azadibenzofuranyl group, an azadibenzothiophenyl group, anazadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolylgroup, an indeno carbazolyl group, and an indolocarbazolyl group, eachunsubstituted or substituted with at least one selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, an n-propylgroup, an isopropyl group, an n-butyl group, a sec-butyl group, anisobutyl group, a tert-butyl group, an ethenyl group, a prophenyl group,a butenyl group, a methoxy group, an ethoxy group, an n-propoxy group,an isopropoxy group, an n-butoxy group, a sec-butoxy group, an isobutoxygroup, and a tert-butoxy group, and the other(s) among R₂, R₃, R₆, andR₇ having no selected substituents and R₁, R₄, R₅, and R₈ to R₁₄ areeach independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, or a substituted or unsubstitutedC₁-C₂₀ alkyl group.
 6. The arylamine compound of claim 5, wherein atleast one selected from R₂, R₃, R₆, and R₇ is selected from groupsrepresented by Formulae 3-1 to 3-16:

wherein, in Formulae 3-1 to 3-16, Y₁₁ is O, S, C(Z₁₃)(Z₁₄), N(Z₁₃), orSi(Z₁₃)(Z₁₄), Z₁₁ to Z₁₄ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkenyl group, a C₁-C₂₀ alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, an anthracenyl group, atriperylenyl group, a pyridinyl group, a pyrimidinyl group, a carbazolylgroup, and a triazinyl group, p3 is an integer from 1 to 3, p4 is aninteger from 1 to 4, p5 is an integer from 1 to 5, p6 is an integer from1 to 6, p9 is an integer from 1 to 9, and * indicates a binding site toa neighboring atom.
 7. The arylamine compound of claim 5, wherein atleast one selected from R₂, R₃, R₆, and R₇ is selected from groupsrepresented by Formulae 4-1 to 4-21:


8. The arylamine compound of claim 1, wherein the compound of Formula 1is represented by one selected from Formulae 2-1 to 2-4:

wherein, in Formulae 2-1 to 2-4, BG is a substituent represented by oneselected from from a group represented by Formulae 3-1 to 3-16:

wherein, in Formulae 3-1 to 3-16, Y₁₁ is O, S, C(Z₁₃)(Z₁₄), N(Z₁₃), orSi(Z₁₃)(Z₁₄), Z₁₁ to Z₁₄ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkenyl group, a C₁-C₂₀ alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, an anthracenyl group, atriperylenyl group, a pyridinyl group, a pyrimidinyl group, a carbazolylgroup, and a triazinyl group, p3 is an integer from 1 to 3, p4 is aninteger from 1 to 4, p5 is an integer from 1 to 5, p6 is an integer from1 to 6, p9 is an integer from 1 to 9, and * indicates a binding site toa neighboring atom.
 9. The arylamine compound of claim 1, wherein thecompound of Formula 1 is represented by one selected from Formulae 2-1to 2-4:

wherein BG in Formulae 2-1 to 2-4 is a substituent represented by oneselected from Formulae 4-1 to 4-21:


10. The arylamine compound of claim 1, wherein reverse intersystemcrossing occurs in the compound due to triplet-triplet annihilation(TTA).
 11. The arylamine compound of claim 1, wherein the arylaminecompound is represented by one selected from Formulae 1 to 16:


12. An organic light-emitting device comprising: a first electrode; asecond electrode facing the first electrode; and an organic layerbetween the first electrode and the second electrode and comprising anemission layer, wherein the organic layer comprises at least onearylamine compound of claim
 1. 13. The organic light-emitting device ofclaim 12, wherein the emission layer comprises the arylamine compound.14. The organic light-emitting device of claim 12, wherein the emissionlayer consists of the arylamine compound.
 15. The organic light-emittingdevice of claim 12, wherein the emission layer further comprises a host,and an amount of the arylamine compound is in a range of about 0.1 partsby weight to about 50 parts by weight based on 100 parts by weight ofthe emission layer.
 16. The organic light-emitting device of claim 12,wherein the arylamine compound comprised in the emission layer is afluorescence emitter having triplet-triplet annihilation (TTA)characteristics, and the emission layer emits TTA fluorescence.
 17. Theorganic light-emitting device of claim 12, wherein the emission layerdoes not comprise an organometallic compound.
 18. The organiclight-emitting device of claim 12, wherein the organic layer furthercomprises a hole transport region between the first electrode and theemission layer and an electron transport region between the emissionlayer and the second electrode.
 19. The organic light-emitting device ofclaim 18, wherein the hole transport region comprises a hole injectionlayer, a hole transport layer, an emission auxiliary layer, an electronblocking layer, or any combination thereof, and the electron transportregion comprises a hole blocking layer, an electron transport layer, anelectron injection layer, or any combination thereof.
 20. An electronicapparatus comprising: the organic light-emitting device of claim 12; anda thin-film transistor, wherein the first electrode of the organiclight-emitting device is in electrical contact with one of a sourceelectrode and a drain electrode of the thin-film transistor.